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Showing NP-Card for Diethyl maleate (NP0337635)

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Record Information
Version2.0
Created at2024-09-11 11:42:38 UTC
Updated at2024-09-11 11:42:38 UTC
NP-MRD IDNP0337635
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiethyl maleate
DescriptionDiethyl fumarate, also known as anti-psoriaticum, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. , It is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. Diethyl fumarate is an extremely weak basic (essentially neutral) compound (based on its pKa). Diethyl fumarate is a banana tasting compound. Outside of the human body,. A maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.P. Diethyl maleate was first documented in 1988 (PMID: 3341033). -10DegreeC) with boiling point 220degreeC at 1 atm (PMID: 1471155) (PMID: 1609410).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337635 (Diethyl maleate)


  Mrv0541 05061310332D          

 12 11  0  0  0  0            999 V2000
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
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3D MOL for NP0337635 (Diethyl maleate)

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3D SDF for NP0337635 (Diethyl maleate)

  Mrv0541 05061310332D          

 12 11  0  0  0  0            999 V2000
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)\C=C/C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-

> <INCHI_KEY>
IEPRKVQEAMIZSS-WAYWQWQTSA-N

> <FORMULA>
C8H12O4

> <MOLECULAR_WEIGHT>
172.1785

> <EXACT_MASS>
172.073558872

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.114787001214324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-diethyl (2Z)-but-2-enedioate

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.4311563566666663

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.533797904472049

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
43.64240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diethyl maleate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337635 (Diethyl maleate)
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PDB for NP0337635 (Diethyl maleate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.310  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9   11                                                  
CONECT    8    6   10   12                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    3    7                                                       
CONECT   12    4    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0337635 (Diethyl maleate)
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SMILES for NP0337635 (Diethyl maleate)
CCOC(=O)\C=C/C(=O)OCC
Download
INCHI for NP0337635 (Diethyl maleate)
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
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Synonyms
ValueSource
2-Butenedioic acid (2Z)-, dimethyl esterChEBI
Maleic acid, diethyl esterChEBI
2-Butenedioate (2Z)-, dimethyl esterGenerator
Maleate, diethyl esterGenerator
Diethyl fumaric acidGenerator
2-Butenedioic acid (2E)-, 1,4-diethyl esterHMDB
2-Butenedioic acid (2E)-, diethyl esterHMDB
2-Butenedioic acid (e)-, diethyl esterHMDB
2-Butenedioic acid (e)-, diethyl ester (9ci)HMDB
2-Butenedioic acid(e)-,diethyl esterHMDB
Anti-psoriaticumHMDB
Diethyl (2E)-2-butenedioateHMDB
Diethyl (2E)-but-2-enedioateHMDB
Diethyl ester OF (e)-2-butenedioic acidHMDB
Diethyl ester(2E)-2-butenedioic acidHMDB
Diethyl ester(e)-2-butenedioic acidHMDB
Diethylester kyseliny fumaroveHMDB
Ethyl fumarateHMDB
Ethyl maleateHMDB
Fumaric acid, diethyl esterHMDB
Fumaric acid, diethyl ester (8ci)HMDB
trans-2-Butenedioic acid diethyl esterHMDB
Diethyl maleic acidGenerator
DiethylmaleateMeSH
Maleic acid, ethyl esterMeSH
Diethyl maleic acid diesterMeSH
Maleic acid diethyl esterMeSH
Ethyl hydrogen maleateMeSH
Monoethyl maleateMeSH
Chemical FormulaC8H12O4
Average Mass172.1785 Da
Monoisotopic Mass172.07356 Da
IUPAC Name1,4-diethyl (2Z)-but-2-enedioate
Traditional Namediethyl maleate
CAS Registry NumberNot Available
SMILES
CCOC(=O)\C=C/C(=O)OCC
InChI Identifier
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-
InChI KeyIEPRKVQEAMIZSS-WAYWQWQTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.34ALOGPS
logP1.43ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.64 m³·mol⁻¹ChemAxon
Polarizability17.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038601  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029781  
KNApSAcK IDNot Available
Chemspider ID4436353  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5271566  
PDB IDNot Available
ChEBI ID68508  
Good Scents IDNot Available
References
General References
  1. Bauman JW, Liu YP, Andrews GK, Klaassen CD: Examination of potential mechanism(s) of metallothionein induction by diethyl maleate. Toxicol Appl Pharmacol. 1992 Dec;117(2):226-32. doi:  10.1016/0041-008x(92)90241-j. [PubMed:1471155  ] 
  2. Bauman JW, McKim JM Jr, Liu J, Klaassen CD: Induction of metallothionein by diethyl maleate. Toxicol Appl Pharmacol. 1992 Jun;114(2):188-96. doi:  10.1016/0041-008x(92)90068-4. [PubMed:1609410  ] 
  3. Yoshida T, Oguro T, Numazawa S, Kuroiwa Y: Effect of diethyl maleate on hepatic ornithine decarboxylase. Toxicol Appl Pharmacol. 1988 Feb;92(2):194-202. doi:  10.1016/0041-008x(88)90379-1. [PubMed:3341033  ]